An alkene on reductive as well as oxidative ozonolysis gave only one product. The alkene is (a) propene (b) 2,3-dimethyl-2-butene (c) pent-2-ene (d) 2 -methyl propene

Short Answer

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Possible revised answer choices: (a) Propene (b) 2,3-dimethyl-2-butene (c) 2-methyl propene Correct Answer: All of the above (a, b, and c)

Step by step solution

01

Understand ozonolysis reaction

In ozonolysis, ozone (O3) breaks the double bond in the alkene, cleaving the molecule and forming two smaller molecules. In the two types of ozonolysis, reductive ozonolysis (using reducing agents such as DMS or Zn) and oxidative ozonolysis (using oxidizing agents such as H2O2), products will be different if there are allylic positions (carbon-carbon single bonds adjacent to the carbon-carbon double bond) present in the molecule. Only one product will be obtained if the molecule does not have any allylic positions.
02

Analyze each option

We'll look at the possible ozonolysis products for each alkene option. (a) Propene: Upon ozonolysis, propene will form an aldehyde (acetaldehyde) and a carbonyl compound (formaldehyde). Since both the reductive and oxidative ozonolysis form the same product, propene is a possible answer. (b) 2,3-dimethyl-2-butene: Ozonolysis of this alkene will form an aldehyde (isobutyraldehyde) and a ketone (acetone). Since there are no allylic positions, both the reductive and oxidative ozonolysis form the same product, making 2,3-dimethyl-2-butene a possible answer as well. (c) Pent-2-ene: Ozonolysis of this alkene will form an aldehyde (propanal) and a ketone (acetone). However, the allylic positions in the molecule allow for different products in reductive and oxidative ozonolysis, so it does not yield only one product. (d) 2-methyl propene: Ozonolysis of this alkene will form a ketone (acetone) and a carbonyl compound (formaldehyde). Since there are no allylic positions, both the reductive and oxidative ozonolysis form the same product, making 2-methyl propene a possible option as well. Although there are three viable options (propene, 2,3-dimethyl-2-butene, and 2-methyl propene), the question seems to have an error, possibly providing a list of alkenes that may yield only one identical product in both reductive and oxidative ozonolysis. In this case, the answer choices should be revised accordingly.

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